From my perspective, from a very humble position, the content on this site seems to skew toward the "harder" science problems lately, a far cry from when 5 out of the top 10 stories were RoR related and many other stories were related to pushing CSS and JS to the extreme with a smattering of stories about startups and people hitting it big or failing.
I think we have since learned about the influence of survivor bias, that you can really accomplish the same things in any programming language and that since YC itself is now focusing on larger problems, some with sociological and political leanings, that it is best to move on from looking at things at the code level and instead look at the bigger picture.
I can empathize and I feel bad for anyone in what feels like a helpless and hopeless situation. I sometimes feel like I am there as well despite having "enough" money for a rainy season or two.
Some people need to hit rock bottom to even begin to understand that there is light at the end of the tunnel. Manual labor, however humiliating and seemingly beneath him, may give him the proper motivation he seems to be lacking.